Esterfication of carboxylic acid with alkyl halide

[Pharmacist]

I have tried to react sodium salt of aliphatic as well as Aromatic sodium carboxylate with non branching primary alkyl bromide.

Solvent was ethanol under reflex conditions.

I am only get my reactants back?!

Can any one tell me what's wrong? 

[chenbeier]

Instead of the sodiumsalt try the silversalt. The equilbrium will go to the ester because of precipitation of AgBr.  Or use Carboxylacid halid with sodiumalkanolate.  

Edited December 28, 2018 by chenbeier

[hypervalent_iodine]

I have used carboxylic acids with Cs₂CO₃ plus alkyl iodides before with some success, but I think the acid chloride / halide route is better if you can manage it.